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SML0656

Rocaglamide

Name: Rocaglamide
Brand: SIGMA

≥96% (HPLC), anti-cancer agent, film

Synonym(s):

(1R,2R,3S,3aR,8bS)-2,3,3a,8b-Tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxamide, NSC 326408, Roc-A, Rocaglamide A

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₁NO₇

CAS Number:

84573-16-0

Molecular Weight:

505.56

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥96% (HPLC)

Form:

film

Quality level:

100

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Product Name

Rocaglamide, ≥96% (HPLC)

Quality Level

100

assay

≥96% (HPLC)

form

film

color

colorless

shipped in

wet ice

storage temp.

−20°C

SMILES string

N(C)(C)C(=O)[C@H]1[C@H]([C@@]2([C@@](Oc5c2c(cc(c5)OC)OC)([C@@H]1c4ccccc4)c3ccc(cc3)OC)O)O

InChI

1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

InChI key

DAPAQENNNINUPW-IDAMAFBJSA-N

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

General description

Rocaglamide is known to be derived from tetrahydro benzofuran and is also an active chemical compound of Aglaia plants.

Application

Rocaglamide has been used as an anticancer drug to treat enterovirus 71 neuropathogenesis and to study the role of prohibitin.

Biochem/physiol Actions

Rocaglamide is associated with osteoblast differentiation. In rheumatoid arthritis, rocaglamide might suppress inflammation, by preventing the expression of cytokines involved in it.

Rocaglamide is a potent anticancer agent isolated from the genus Aglaia. Rocaglamides inhibit protein synthesis without affecting DNA or RNA synthesis. Recent study shows that Rocaglamide binds to prohibitin (PHB) 1 and 2, which prevents interaction between PHB and CRaf and inhibits CRaf activation and subsequently CRaf-MEK-ERK signaling. Also, Rocaglamide is an immunosuppressant that inhibits activation of NF-kB and NF-AT.

Rocaglamide is a potent anticancer agent.

Features and Benefits

This compound is featured on the MAPKKKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000383537

0000189946

0000139551

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The traditional Chinese herbal compound rocaglamide preferentially induces apoptosis in leukemia cells by modulation of mitogen-activated protein kinase activities.

Jia Y Zhu et al.

International journal of cancer, 121(8), 1839-1846 (2007-06-15)

With an increasing cancer rate worldwide, there is an urgent quest for the improvement of anticancer drugs. One of the main problems of present chemotherapy in treatment of tumor patients is the toxicity of drugs. Most of the existent anticancer

Prohibitin plays a critical role in Enterovirus 71 neuropathogenesis.

Too I H K, et al.

PLoS Pathogens, 14(1), e1006778-e1006778 (2018)

New insecticidal rocaglamide derivatives and related compounds from Aglaia oligophylla.

M Dreyer et al.

Journal of natural products, 64(4), 415-420 (2001-04-28)

Organic-soluble extracts of the twigs of Aglaia oligophylla collected in Vietnam yielded four insecticidal cyclopentatetrahydrobenzofurans of the rocaglamide type including one new natural product (compound 4). Moreover, two cyclopentatetrahydrobenzopyran derivatives, belonging to the aglain and aglaforbesin types, respectively, were also

Stereoselective synthesis of the rocaglamide skeleton via a silyl vinylketene formation/[4 + 1] annulation sequence.

Matthew W Giese et al.

Organic letters, 10(19), 4215-4218 (2008-08-30)

The tricyclic core of the cyclopentabenzofurans has been prepared in an efficient and stereoselective manner utilizing an intramolecular silyl vinylketene formation/[4 + 1] annulation sequence. This novel approach affords the ABC ring system where the adjacent phenyl and aryl substituents

Potential of cyclopenta[b]benzofurans from Aglaia species in cancer chemotherapy.

Soyoung Kim et al.

Anti-cancer agents in medicinal chemistry, 6(4), 319-345 (2006-07-18)

During the past few years, a group of cyclopenta[b]benzofurans from the plant genus Aglaia has received broad scientific attention as interesting natural product lead compounds with potential anticancer and insecticidal activities. Since the first cyclopenta[b]benzofuran derivative, rocaglamide, from Aglaia elliptifolia

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Articles

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

Global Trade Item Number

SKU	GTIN
SML0656-100UG	04061832450490

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